[go: up one dir, main page]

US20170247647A1 - Flavor nanoemulsions and methods of preparing the same - Google Patents

Flavor nanoemulsions and methods of preparing the same Download PDF

Info

Publication number
US20170247647A1
US20170247647A1 US15/518,595 US201515518595A US2017247647A1 US 20170247647 A1 US20170247647 A1 US 20170247647A1 US 201515518595 A US201515518595 A US 201515518595A US 2017247647 A1 US2017247647 A1 US 2017247647A1
Authority
US
United States
Prior art keywords
flavor
nanoemulsion
lecithin
fatty acid
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US15/518,595
Other languages
English (en)
Inventor
Daniel Kaiping Lee
Chii-Fen Wang
Ying Yang
Daniel Vaccari
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by International Flavors and Fragrances Inc filed Critical International Flavors and Fragrances Inc
Priority to US15/518,595 priority Critical patent/US20170247647A1/en
Assigned to INTERNATIONAL FLAVORS AND FRAGRANCES INC. reassignment INTERNATIONAL FLAVORS AND FRAGRANCES INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Vaccari, Daniel, Lee, Daniel Kaiping, YANG, YING, WANG, CHII-FEN
Publication of US20170247647A1 publication Critical patent/US20170247647A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • A23L2/56—Flavouring or bittering agents
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2026—Hydroxy compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/34—Sugar alcohols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/80—Emulsions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/03—Organic compounds
    • A23L29/035—Organic compounds containing oxygen as heteroatom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A23L29/231—Pectin; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A23L29/238—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin from seeds, e.g. locust bean gum or guar gum
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
    • A23L29/25—Exudates, e.g. gum arabic, gum acacia, gum karaya or tragacanth
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/269—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of microbial origin, e.g. xanthan or dextran
    • A23L29/27—Xanthan not combined with other microbial gums
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
    • C12G3/00—Preparation of other alcoholic beverages
    • C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
    • C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/184—Emulsifier
    • A23V2250/1842—Lecithin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/184—Emulsifier
    • A23V2250/1846—Phosphatidyl Choline
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/50—Polysaccharides, gums
    • A23V2250/502—Gums
    • A23V2250/5022—Acacia
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/50—Polysaccharides, gums
    • A23V2250/502—Gums
    • A23V2250/506—Guar
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/50—Polysaccharides, gums
    • A23V2250/502—Gums
    • A23V2250/5072—Pectine, pectinate
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/50—Polysaccharides, gums
    • A23V2250/502—Gums
    • A23V2250/5086—Xanthan
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
    • A23V2250/64—Sugar alcohols
    • A23V2250/6402—Erythritol
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
    • A23V2250/64—Sugar alcohols
    • A23V2250/6412—Isomaltitol, palatinit
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
    • A23V2250/64—Sugar alcohols
    • A23V2250/6418—Mannitol
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
    • A23V2250/64—Sugar alcohols
    • A23V2250/642—Sorbitol
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/60—Sugars, e.g. mono-, di-, tri-, tetra-saccharides
    • A23V2250/64—Sugar alcohols
    • A23V2250/6422—Xylitol

Definitions

  • Flavor nanoemulsions have been used to create optically clear beverages containing hydrophobic flavor oils. Surfactants are added to facilitate the formation of nanoemulsions and also stabilize these nanoemulsions.
  • US Patent Application Publication 2009/0285952 discloses a nanoemulsion composition containing an enzyme-degraded lecithin for use in alcoholic drinks or carbonated drinks.
  • Japanese Application 2003/284510 describes a composition having alcohol resistance in which a polyglyceryl fatty acid ester and sucrose fatty acid ester were used as surfactants. However, this composition was considered unsatisfactory to flavors due to the surfactants contained therein. See US2009/0285952.
  • Japanese Patent 05588048 discloses a flavor emulsion composition useful for alcoholic beverages and containing hydrophilic polyglyceryl fatty acid ester, lipophilic polyglyceryl fatty ester, and lysolecithin.
  • This invention is based on the discovery that flavor nanoemulsions prepared from a polyethoxylated sorbitan fatty acid ester and a lecithin are stable and optically clear in liquid beverages including alcoholic beverages.
  • one aspect of this invention relates to a flavor nanoemulsion comprising a plurality of oil droplets, an aqueous phase, and a surfactant system.
  • the nanoemulsion has a water activity of 0.7 or less (e.g., 0.65 or less and 0.6 or less) and has a water content of 25% or less (e.g., 20% or less and 15% or less) by weight of the nanoemulsion.
  • Each of the oil droplets contains a flavor and disperses in the aqueous phase.
  • the oil droplets each can contain an oil-soluble vitamin, an oil-soluble colorant, an antioxidant, a taste modulator, a mouthfeel modulator, or a combination thereof.
  • Exemplary taste modulators are acid maskers, cooling agents, hot tasting substances, sweet enhancers, salt enhancers, salivation-inducing substances, substances causing a warmth or tingling feeling, and combinations thereof.
  • the aqueous phase contains water and a co-solvent.
  • Typical co-solvent is polyols including propylene glycol, 1.3-propandiol, glycerin, butylene glycol, erythritol, xylitol, mannitol, sorbitol, isomalt, and combinations thereof.
  • the co-solvent is a mixture of propylene glycol, glycerin, and sorbitol.
  • propylene glycol is present at a level of 5 to 25%
  • glycerin is present at a level of 0.1 to 35%
  • sorbitol is present at a level of 25 to 65%, all by weight of the flavor nanoemulsion.
  • the weight ratio between water and the co-solvent is 1:95 to 1:3, preferably 1:40 to 1:4, and more preferably 1:20 to 1:5.
  • the surfactant system includes a polyethoxylated sorbitan fatty acid ester and a lecithin. It can be at a level of 0.1 to 20% and the flavor can be at a level of 1 to 20%, both by the weight of the flavor nanoemulsion.
  • the polyethoxylated sorbitan fatty acid ester has an HLB of 9 to 20.
  • examples include polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, and a combination thereof.
  • the lecithin having an HLB of 4 to 16 can be native, deoiled, fractionated, or enzyme-modified.
  • the weight ratio between the polyethoxylated sorbitan fatty acid ester and the lecithin is 30:1 to 1:5.
  • the polyethoxylated sorbitan fatty acid ester is typically present at a level of 0.05 to 15%, and the lecithin is typically present at a level of 0.05 to 5%, both by weight of the flavor nanoemulsion.
  • Any flavor nanoemulsion described above can further contain a defoamer selected from the group consisting of a silicone emulsion antifoamer, polydimethylsiloxane antifoamer, 2-octanol, petrolatum, hop lipid, alginate, mineral oil, sorbitan monostearate, and a combination thereof.
  • a defoamer selected from the group consisting of a silicone emulsion antifoamer, polydimethylsiloxane antifoamer, 2-octanol, petrolatum, hop lipid, alginate, mineral oil, sorbitan monostearate, and a combination thereof.
  • liquid beverage or liquid beverage concentrate containing any of the flavor nanoemulsions described above.
  • the liquid beverage or liquid beverage concentrate having a turbidity of 10 NTU or less (e.g., 5 NTU or less, 3 NTU or less, and 2 NTU or less), contains alcohol from 1 to 60% (e.g., 2-30%).
  • the method include the steps of: (a) providing an aqueous phase containing a polyethoxylated sorbitan fatty acid ester, water, and a co-solvent, (b) providing an oil phase containing a flavor and a lecithin, and (c) emulsifying the oil phase into the aqueous phase, thereby obtaining the nanoemulsion.
  • the polyethoxylated sorbitan fatty acid ester has an HLB of 9 to 20, and the lecithin has an HLB of 4 to 16.
  • the polyethoxylated sorbitan fatty acid ester, co-solvent, and lecithin are defined above.
  • free fatty acid refers to the fatty acid containing a free carboxyl group (—COOH). Free fatty acids include their salts and solvates.
  • flavoring compounds in beverage preparation are essential oils such as orange, lemon, and grapefruit, which have limited water solubility. Flavor emulsions that result in optically clear beverages are of increasing interest in the beverage industry. Desirable flavor emulsions (a mean particle size of 200 nanometers or less) are visually translucent and thermodynamically stable.
  • flavor nanoemulsions are optically clear and maintain a high stability in alcoholic beverages.
  • These flavor nanoemulsions can be readily prepared from a surfactant system containing at least a polyethoxylated sorbitan fatty acid ester and a lecithin.
  • the flavor nanoemulsions of this invention are typically oil-in-water systems each having a plurality of oil droplets, a continuous aqueous phase, a surfactant system, and, optionally, a defoamer.
  • the oil droplets are normally hydrophobic and immiscible with water. They contain one or more active materials selected from flavors, oil-soluble vitamins, oil-soluble colorants, antioxidants, taste modulators, mouthfeel modulators, oil-soluble defoamer, and any combinations thereof.
  • Useful taste modulators include acid maskers, polyaldo matric, beer hops, cooling agents, hot tasting substances, sweet enhancers, salt enhancers, salivation-inducing substances, substances causing a warmth or tingling feeling, and any combinations thereof.
  • Exemplary mouthfeel modulators are coconut oil, coconut milk with or without sugar, vanillin, stevia glycosides such as Rebaudiosides A, C, D, E, and F, medium chain tryglycerides, steviol, glucosylated stevia glycosides, and combinations thereof.
  • Suitable active materials include fragrances, pro-fragrances, malodor counteractive agents, anti-inflammatory agents, fungicides, anesthetics, analgesics, antimicrobial actives, anti-viral agents, anti-infectious agents, anti-acne agents, skin lightening agents, insect repellants, emollients, skin moisturizing agents, wrinkle control agents, UV protection agents, fabric softener actives, hard surface cleaning actives, skin or hair conditioning agents, insect repellants, animal repellents, vermin repellents, flame retardants, antistatic agents, nanometer size inorganic solids, polymeric or elastomeric particles, and any combinations thereof.
  • the oil droplets can also contain adjunct materials such as viscosity modifiers and pH modifiers.
  • adjunct materials such as viscosity modifiers and pH modifiers. The active materials and the adjunct materials are described below in more details.
  • the flavor is present at a level of 0.1 to 20% (e.g., 0.2 to 15% and 0.5 to 10%) by weight of the flavor nanoemulsion.
  • the oil droplets each have a droplet size of 500 nm or below, e.g., 200 nm or below, 100 nm or below, 0.1 to 500 nm, 0.1 to 200 nm, and 1 to 100 nm.
  • the oil droplets are dispersed in the aqueous phase that contains water and a co-solvent.
  • the co-solvent is added to improve the solubility of the surfactant system in water and also the stability of the nanoemulsion.
  • Exemplary co-solvents are polyols selected from the group consisting of propylene glycol, 1,3-propandiol, glycerin, butylene glycol, erythritol, xylitol, mannitol, sorbitol, isomalt, or a combination thereof.
  • the flavor nanoemulsion contains an aqueous phase having a co-solvent that is a mixture of propylene glycol, glycerin, and sorbitol.
  • propylene glycol can be present at a level of 5 to 25% (e.g., 5 to 20%), glycerin is present at a level of 0.1 to 35% (e.g., 5 to 30%), and sorbitol is present at a level of 25 to 65% (e.g., 30 to 50%), all by weight of the flavor nanoemulsion.
  • the weight ratio between water and the polyol is 1:95 to 1:2 (e.g., 1:95 to 1:3, 1:95 to 1:4, 1:50 to 1:3, and 1:20 to 1:5).
  • the surfactant system is contained in the oil phase, the aqueous phase, or both. It is present at a level of 0.1 to 20% (e.g., 0.2 to 20%, 0.3 to 15%, and 0.5 to 12%) by weight of the nanoemulsion.
  • Suitable surfactant systems have at least two surfactants: a polyethoxylated sorbitan fatty acid ester and a lecithin.
  • the weight ratio between the polyethoxylated sorbitan fatty acid ester and the lecithin is 30:1 to 1:5 (e.g., 25:1 to 1:2 and 20:1 to 1:1).
  • Useful polyethoxylated sorbitan fatty acid esters have an HLB of 9 to 20, preferably 13 to 20, and more preferably, 14 to 18.
  • HLB refers to the “hydrophilic-lipophilic balance” of a molecule.
  • the HLB number indicates the polarity of the molecules in a range of 1-40, with the most commonly used emulsifiers having a value between 1 and 20.
  • the HLB number increases with increasing hydrophilicity.
  • the HLB of a surfactant can be determined by calculating values for the different regions of the molecule, as described by Griffin, “Classification of Surface-Active Agents by ‘HLB,’” Journal of the Society of Cosmetic Chemists 1 (1949), 311-26; and Griffin, “Calculation of HLB Values of Non-Ionic Surfactants,” Journal of the Society of Cosmetic Chemists 5 (1954), 249-56.
  • Suitable polyethoxylated sorbitan fatty acid esters include polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, and polyoxyethylene sorbitan monooleate.
  • the number of repetitive oxyethylene —(CH 2 CH 2 —O)— can be in the range of 2 to 1000 (e.g., 5 to 100, 10 to 50, 10 to 30, and 20).
  • Commercially available polyethoxylated sorbitan fatty acid esters are those under the name TweenTM by ICI Americas, Inc. (Wilmington, Del.), e.g., TweenTM 60 (HLB of 14.9), TweenTM 80 (HLB of 15), and TweenTM 20 (HLB of 16.7). They have 20 repetitive oxyethylene units.
  • the polyethoxylated sorbitan fatty acid ester is present at a level of 0.05 to 15% (e.g., 0.1 to 12%, 0.15 to 10%, and 0.2 to 8%) by weight of the flavor nanoemulsion.
  • the weight ratio of the polyethoxylated sorbitan fatty acid ester and the flavor can be in the range of 1:15 to 3:1 (e.g., 1:10 to 2.5:1 and 1:10 to 2:1).
  • Useful lecithins have an HLB ranging from 4 to 16 (e.g., 6-16 and 8-16). These lecithins can be native, deoiled, fractionated, or enzyme-modified. Native and standard liquid lecithins have an HLB of 4 to 8 and enzyme modified lecithins (“lysolecithin”) have an HLB of 8 to 16.
  • Lecithins are mixtures of two primary components, namely phospholipids and triglycerides, with minor amounts of other constituents such as phytoglycolipids, phytosterols, tocopherols, and fatty acids.
  • Phospholipids in lecithin include phosphatidylcholines, phosphatidylethanolamine, phosphatidylserine, phosphatidic acid, phosphatidylglycerol, and phosphatidylinositol.
  • Phosphatidylcholines can be enzymatically modified to form lysophosphatidylcholines. Both phosphatidylcholines and lysophosphatidylcholines are desirable surfactants contained in lecithins.
  • Lecithins are prepared by extracting and purifying phospholipids from naturally occurring products including, but not limited to, soybeans, eggs, sunflower or rapeseed (canola) seeds, milk, marine sources, and cottonseeds.
  • Food-grade lecithins are available in liquid, granular and powder from commercial sources and include, e.g., ALCOLEC Lecithins sold by American Lecithin Company (Oxford, CT) and TOPCITHIN, LECIPRIME, LECISOY, EMULFLUID, METARIN, EMULPUR, LECIGRAN, EPIKURON, LECIMULTHIN, EMULTOP, and OVOTHIN Lecithins sold by CARGILL (Mechelen, Belgium), and SOLEC Lecithins sold by DuPont Nutrition & Health (St. Louis, Mo.).
  • Lecithins may be deoiled (i.e., having 3% or less residual oil) or fractionated (i.e., separating soluble components and insoluble components in a solvent, which can be an alcohol such as ethanol or an ethanol-water mixture).
  • a lecithin is mixed with an alcohol (such as ethanol or ethanol-water).
  • Phosphatidylcholine has a good solubility in ethanol, whereas most other phospholipids do not dissolve well.
  • the ethanol phase is separated from the lecithin sludge. Removal of ethanol yields a phosphatidylcholine-enriched lecithin.
  • phosphatidylcholine and lysophosphatidylcholine are present at a level of 20% or greater by weight of the lecithin.
  • free fatty acids are also present in lecithins. It is desirable that their level is 15% or less by weight of the lecithin (e.g., 10% or less, and 5% or less).
  • lecithin refers to both a single type of lecithin (e.g., native, deoiled, fractionated, or enzyme modified) as well as to a mixture of lecithins.
  • the lecithin can be present at a level of 0.05 to 15% (e.g., 0.1 to 10% and 0.2 to 5%) by weight of the flavor nanoemulsion.
  • other food safe surfactants can also be added to the flavor nanoemulsions of this invention.
  • examples include ammonium phosphatides, mono- or diglycerides of fatty acids including distilled monoglycerides, acetic acid esters of mono- and diglycerides (Acetem), lactic acid esters of mono- and diglycerides of fatty acids (Lactem), citric acid esters of mono and diglycerides of fatty acids (Citrem), mono and diacetyl tartaric acid esters of mono and diglycerides of fatty acids (Datem), succinic acid esters of monoglycerides of fatty acids (SMG), ethoxylated monoglycerides, sucrose esters of fatty acids, sucroglycerides, polyglycerol esters of fatty acids, polyglycerol polyricinoleate, propane-1,2 diol esters of fatty acids, thermally
  • sorbitan esters of fatty acids examples include sorbitan monostearate, sorbitan tristearate, sorbitan monolaurate, sorbitan monooleate, sorbitan monopalmitate, and saccharose esters of fatty acids.
  • the flavor nanoemulsion contains a defoamer, which can be a water-dispersible defoamer or oil-soluble defoamer.
  • a defoamer which can be a water-dispersible defoamer or oil-soluble defoamer.
  • examples include silicone emulsion antifoamers, polydimethylsiloxane antifoamers, 2-octanol, petrolatum, hop lipids, alginates, mineral oil, sorbitan monostearate, and a combination thereof.
  • the flavor nanoemulsions described above appear translucent or optically clear. They can be added to an alcoholic or non-alcoholic, carbonated or non-carbonated beverage base solution to enhance the flavor, taste, or mouthfeel of the beverage. When a clear beverage base solution is used, the final beverage remains optically clear while receiving the benefit of taste enhancement by introducing a nanoemulsion of this invention.
  • translucent refers to a nanoemulsion that can be seen through, although the light may be diffused by the material itself.
  • the nanoemulsion of the present invention provides a clear soft drink beverage.
  • clear or “optically clear” (transparent) refers to a nanoemulsion or beverage having a turbidity of less than 10 Nephelometric Turbidity Units (“NTU;” e.g., less than 5 NTU and less than 3 NTU).
  • NTU Nephelometric Turbidity Units
  • Turbidity can be measured following the procedures well known in the art, e.g., Fernandez et al., Food Chemistry (2000), 71, 563-66; and Christensen et al., Journal—American Water Works Association (2003), 95, 179-189.
  • the flavor nanoemulsions of this invention have a relatively low level of water. Some flavor nanoemulsions contain water 25% or less (e.g., 20% or less, 15% or less, 1 to 20%, 5-20%). The flavor nanoemulsions each have a water activity of 0.7 or less (e.g., 0.65 or less, 0.6 or less, and 0.55 or less).
  • Water activity is the ratio between the vapor pressure of the flavor nanoemulsion, when in a completely undisturbed balance with the surrounding air media, and the vapor pressure of distilled water under identical conditions.
  • a water activity of 0.7 means the vapor pressure is 70 percent of that of pure water.
  • pure distilled water has a water activity of exactly one. As temperature increases, water activity typically increases.
  • Bacteria usually require at least a water activity of 0.91, and fungi at least 0.7.
  • the flavor nanoemulsions of this invention will not support the growth of microorganisms. As such, the flavor nanoemulsions usually are free of a preservative.
  • the flavor nanoemulsion further contains, in the aqueous phase, 0.01% to 20% a carrier material including mono- and di-saccharide sugars such as glucose, lactose, levulose, trehalose, fructose, maltose, ribose, sucrose, or a combination thereof.
  • the aqueous phase further contains a protein, gum, and/or hydrocolloid.
  • Suitable proteins include soy protein isolate, soy protein concentrate, whey protein isolate, whey protein concentrate, gelatin, pea protein, and protein hydrolysates.
  • gums and hydrocolloids include xanthan gum, guar gum, gum acaia, chemically modified gum acaia, pectin, and alginate.
  • Flavor nanoemulsions of the present invention are prepared by emulsifying the flavor oil into the aqueous phase in the presence of polyethoxylated sorbitan fatty acid ester and lecithin using conventional techniques. Briefly, nanoemulsions are typically prepared by mixing the aqueous and oil phases, and subjecting the mixture to homogenization several times, or, in the terminology of the art, to make more than one “pass.”
  • a pre-emulsion step i.e., a high shear mixing step
  • the speed of high shear mixing may range from 3,000 rpm to 20,000 rpm and the time of mixing may range from 5 to 30 minutes.
  • a high-pressure homogenizer e.g., commercially available Niro Panda 2000
  • other type of homogenizer e.g., MICROFLUIDIZER commercially available from Microfluidics or EMULSIFLEX commercially available from Avestin
  • Homogenization can be carried out at 3,000/300 psi to 10,000/1,000 psi using a two-stage homogenizer for two, three, or more passes; or 6,500/500 psi to 20,000/2,000 psi for one, two or more passes.
  • the instant flavor nanoemulsion can be used in a variety of consumer, food, or pharmaceutical products.
  • the flavor nanoemulsion finds application in gums, confections, oral care products, beverages, snacks, dairy products, soups, sauces, condiments, detergents, fabric softeners and other fabric care products, antiperspirants, deodorants, talc, kitty litter, hair care and styling products, personal care products, air fresheners, cereals, baked goods and cleaners.
  • the instant flavor nanoemulsion is used in beverages and beverage liquid concentrates. Accordingly, in addition to flavor nanoemulsions, the present invention also provides optically clear final beverage products or liquid beverage concentrates containing the flavor nanoemulsion of the invention.
  • the instant flavor nanoemulsion is dosed at a level between 1 ppm to 60% (e.g., 1 ppm to 20% and 5 ppm to 5%) by weight of the final beverage product so that the product contains a flavor oil 0.01 ppm to 10% (0.1 ppm to 5%, 0.5 ppm to 1%, and 1 ppm to 100 ppm).
  • the final beverage product thus prepared is clear, having a turbidity of 10 NTU (e.g., 5 NTU and 3 NTU) or below.
  • liquid beverage concentrate means a liquid composition that can be diluted with another liquid, such as an aqueous, potable liquid to provide a final beverage or added to a food product prior to being consumed.
  • liquid refers to a non-gaseous, flowable, fluid composition at room temperature (i.e., 70° F.).
  • final beverage as used herein means a beverage that has been prepared either by the standard soft drink (i.e., ready-to-drink) preparation procedure or by diluting the concentrate to provide a beverage in a potable, consumable form.
  • the concentrate is non-potable due to acidulant content and/or flavor intensity.
  • concentration a concentration of 75 times (i.e., “75 ⁇ ”) would be equivalent to 1 part concentrate to 74 parts water (or other potable liquid) to provide the final beverage.
  • concentration the flavor profile of the final beverage is taken into account when determining an appropriate level of dilution, and thus concentration, of the liquid beverage concentrate.
  • the dilution factor of the concentrate can also be expressed as the amount necessary to provide a single serving of concentrate.
  • a moderately concentrated product may be formulated to be diluted by a factor of at least 5 times to provide a final beverage, which can be, for example, an 8 ounce beverage.
  • the concentrate is formulated to be diluted by a factor of 5 to 15 times to provide a final beverage.
  • the liquid concentrate has a pH of 1.8 to 4, or more particularly, 1.8 to 2.9, 2 to 3.1, or 2 to 2.5; and a viscosity of 7.5 to 100 cP, 10 to 100 cP, 15 to 100 cP, 10 to 50 cP, or 10 to 20 cP, as measured using Spindle S00 at 50 rpm and 20° C. with a Brookfield DVII+Pro Viscometer.
  • the concentrate includes at least 0.1 to 15 percent acidulant by weight of the concentrate.
  • Any edible, food grade organic or inorganic acid such as, but not limited to, citric acid, malic acid, succinic acid, acetic acid, hydrochloric acid, adipic acid, tartaric acid, fumaric acid, phosphoric acid, lactic acid, sodium acid pyrophosphate, salts thereof, and combinations thereof can be used, if desired.
  • the selection of the acidulant may depend, at least in part, on the desired pH of the concentrate and/or taste imparted by the acidulant to the diluted final beverage.
  • the amount of acidulant included in the concentrate may depend on the strength of the acid.
  • a buffer can be added to the concentrate to provide for increased acid content at a desired pH.
  • Suitable buffers include, for example, a conjugated base of an acid, gluconate, acetate, phosphate or any salt of an acid (e.g., sodium citrate and potassium citrate).
  • an undissociated salt of the acid can buffer the concentrate.
  • the beverages or concentrates of the invention can include one or more juices or juice concentrates (such as at least a 4 ⁇ concentrated product) from fruits or vegetables for bulk solid addition.
  • the juice or juice concentrate may include, for example, coconut juice (also commonly referred to as coconut water), apple, pear, grape, orange, potato, tangerine, lemon, lime, tomato, carrot, beet, asparagus, celery, kale, spinach, pumpkin, strawberry, raspberry, banana, blueberry, mango, passionfruit, peach, plum, papaya, and combinations.
  • coconut juice also commonly referred to as coconut water
  • apple pear, grape, orange, potato, tangerine, lemon, lime, tomato, carrot, beet, asparagus, celery, kale, spinach, pumpkin, strawberry, raspberry, banana, blueberry, mango, passionfruit, peach, plum, papaya, and combinations.
  • the juice or juice concentrates may also be added as a puree, if desired.
  • concentrates can be added to potable liquids to form flavored beverages.
  • the concentrate may be non-potable (such as due to the high acid content and intensity of flavor).
  • the beverage concentrate can be used to provide flavor to water, cola, carbonated water, tea, coffee, seltzer, club soda, the like, and can also be used to enhance the flavor of juice.
  • the beverage concentrate can be used to provide flavor to alcoholic beverages, including but not limited to flavored champagne, sparkling wine, wine spritzer, cocktail, martini, or the like.
  • the concentrate is used in an optically clear beverage.
  • Beverage concentrates can also be combined with a variety of food products to add flavor to the food products.
  • concentrates can be used to provide flavor to a variety of solid, semi-solid, and liquid food products, including but not limited to oatmeal, cereal, yogurt, strained yogurt, cottage cheese, cream cheese, frosting, salad dressing, sauce, and desserts such as ice cream, sherbet, sorbet, and Italian ice.
  • Appropriate ratios of the beverage concentrate to food product or beverage can readily be determined by one of ordinary skill in the art.
  • stability is defined as a flavor quality and intensity that remains acceptable for use in end use applications.
  • a stable emulsion has a shelf-life of at least 1 year to three years depending on storage conditions.
  • a nanoemulsion refers to lipid droplets in size of 200 nanometers or less (e.g., 50 to 150 nanometers) in diameter. See Mason et al. 2006, J. Physics: Condensed Matter 18, 635-66. Nanoemulsions are produced by mixing a water-immiscible oil phase into an aqueous phase with a high-stress mechanical process.
  • Flavor oils suitable for preparing the nanoemulsions of this invention contain one or more volatile and nonvolatile compounds.
  • a variety of flavors can be used in accordance with the present invention. Flavors may be chosen from synthetic flavors, flavoring oils and oil extracts derived from plants, leaves, flowers, fruits, and combinations thereof.
  • Representative flavor oils include, but are not limited to, spearmint oil, cinnamon oil, peppermint oil, clove oil, bay oil, thyme oil, cedar leaf oil, oil of nutmeg, oil of sage, and oil of bitter almonds.
  • artificial, natural or synthetic fruit flavors such as vanilla, chocolate, coffee, cocoa and citrus oil, including lemon, orange, grape, lime and grapefruit, and fruit essences including apple, pear, peach, strawberry, watermelon, raspberry, cherry, plum, pineapple, apricot and so forth. These flavors can be used individually or in admixture.
  • Volatile compounds in the flavor oils may include, but are not limited to, acetaldehyde, dimethyl sulfide, ethyl acetate, ethyl propionate, methyl butyrate, and ethyl butyrate.
  • Flavors containing volatile aldehydes or esters include, e.g., cinnamyl acetate, cinnamaldehyde, citral, diethylacetal, dihydrocarvyl acetate, eugenyl formate, and p-methylanisole.
  • volatile compounds that may be present in the flavor oils include acetaldehyde (apple); benzaldehyde (cherry, almond); cinnamic aldehyde (cinnamon); citral, i.e., alpha citral (lemon, lime); neral, i.e., beta citral (lemon, lime); decanal (orange, lemon); ethyl vanillin (vanilla, cream); heliotropine, i.e., piperonal (vanilla, cream); vanillin (vanilla, cream); alpha-amyl cinnamaldehyde (spicy fruity flavors); butyraldehyde (butter, cheese); valeraldehyde (butter, cheese); citronellal (modifies, many types); decanal (citrus fruits); aldehyde C-8 (citrus fruits); aldehyde C-9 (citrus fruits); aldehyde C-12 (citor
  • the flavor nanoemulsion can further contain the following active materials:
  • taste masking agents substances for masking one or more unpleasant taste sensations, in particular a bitter, astringent and/or metallic taste sensation or aftertaste.
  • Examples include lactisol [2O-(4-methoxyphenyl) lactic acid] (cf. U.S. Pat. No. 5,045,336), 2,4-dihydroxybenzoic acid potassium salt (cf. U.S. Pat. No. 5,643,941), ginger extracts (cf. GB 2,380,936), neohesperidine dihydrochalcone (cf. Manufacturing Chemist 2000, July issue, p. 16-17), specific flavones (2-phenylchrom-2-en-4-ones) (cf. U.S. Pat.
  • nucleotides for example cytidine-5′-monophosphates (CMP) (cf. US 2002/0177576), specific sodium salts, such as sodium chloride, sodium citrate, sodium acetate and sodium lactate (cf. Nature, 1997, Vol. 387, p. 563), a lipoprotein of .beta.-lactoglobulin and phosphatidic acid (cf. EPA 635 218), neodiosmine [5,7-dihydroxy-2-(4-methoxy-3-hydroxyphenyl)-7-O-neohesperidosyl-chrom-2-en-4-one] (cf. U.S. Pat. No.
  • hydroxyflavanones according to EP 1 258 200, in turn preferred in this respect 2-(4-hydroxyphenyl)-5,7-dihydroxychroman-4-one (naringenin), 2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-4-one (eriodictyol), 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychroman-4-one (eriodictyol-7-methylether), 2-(3,4-dihydroxyphenyl)-7-hydroxy-5-methoxychroman-4-one (eriodictyol-5-methylether) and 2-(4-hydroxy-3-methoxyphenyl)-5,7-dihydroxychroman-4-one (homoeriodictyol), the (2S)- or (2R)-enantiomers thereof or mixtures thereof as well as the mono- or polyvalent phenolate salts thereof with Na + , K + , NH4 + , Ca 2
  • taste sensates including hot tasting, salivation-inducing substances, substances causing a warmth or tingling feeling, and cooling active ingredients.
  • hot tasting and/or salivation-inducing substances and/or substances which cause a feeling of warmth and/or a tingling feeling on the skin or on the mucous membranes and which can be a constituent of the products according to the invention are: capsaicin, dihydrocapsaicin, gingerol, paradol, shogaol, piperine, carboxylic acid-N-vanillylamides, in particular nonanoic acid-N-vanillylamide, pellitorin or spilanthol, 2-nonanoic acid amides, in particular 2-nonanoic acid-N-isobutylamide, 2-nonanoic acid-N-4-hydroxy-3-methoxyphenylamide, alkyl ethers of 4-hydroxy-3-methoxybenzyl alcohol, in particular 4-hydroxy-3-methoxybenzyl-n-but
  • Examples of preferred hot tasting natural extracts and/or natural extracts which cause a feeling of warmth and/or a tingling feeling on the skin or on the mucous membranes and which can be a constituent of the products according to the invention are: extracts of paprika, extracts of pepper (for example capsicum extract), extracts of chili pepper, extracts of ginger roots, extracts of Aframomum melgueta, extracts of Spilanthes-acmella, extracts of Kaempferia galangal or extracts of Alpinia galanga.
  • Suitable cooling active ingredients include the following: 1-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat®MGA), menthyl lactate (trade name: Frescolat®ML, menthyl lactate preferably being 1-menthyl lactate, in particular 1-menthyl-1-lactate), substituted menthyl-3-carboxamides (for example menthyl-3-carboxylic acid-N-ethylamide), 2-isopropyl-N-2,3-trimethyl-butanamide, substituted cyclohexane carboxamides, 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate, N-acetylglycine menthyl ester, isopulegol, hydroxycarboxylic acid menthyl esters (for example menthyl-3-hydroxybutyrate), monomenth
  • Cooling active ingredients which are particularly preferred are as follows: 1-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat®MGA), menthyl lactate (preferably 1-menthyl lactate, in particular 1-menthyl-1-lactate, trade name: Frescolat®ML), 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate.
  • vitamins including any vitamin, a derivative thereof and a salt thereof examples are as follows: vitamin A and its analogs and derivatives (e.g., retinol, retinal, retinyl palmitate, retinoic acid, tretinoin, and iso-tretinoin, known collectively as retinoids), vitamin E (tocopherol and its derivatives), vitamin C (L-ascorbic acid and its esters and other derivatives), vitamin B3 (niacinamide and its derivatives), alpha hydroxy acids (such as glycolic acid, lactic acid, tartaric acid, malic acid, citric acid, etc.) and beta hydroxy acids (such as salicylic acid and the like);
  • vitamin A and its analogs and derivatives e.g., retinol, retinal, retinyl palmitate, retinoic acid, tretinoin, and iso-tretinoin, known collectively as retinoids
  • vitamin E tocopherol and its derivatives
  • vitamin C L
  • antibacterials including bisguanidines (e.g., chlorhexidine digluconate), diphenyl compounds, benzyl alcohols, trihalocarbanilides, quaternary ammonium compounds, ethoxylated phenols, and phenolic compounds, such as halo-substituted phenolic compounds, like PCMX (i.e., p-chloro-m-xylenol), triclosan (i.e., 2,4,4′-trichloro-2′ hydroxy-diphenylether), thymol, and triclocarban;
  • PCMX i.e., p-chloro-m-xylenol
  • triclosan i.e., 2,4,4′-trichloro-2′ hydroxy-diphenylether
  • antioxidants such as beta-carotene, vitamin C (Ascorbic Acid) or an ester thereof, vitamin A or an ester thereof, vitamin E or an ester thereof, lutein or an ester thereof, lignan, lycopene, selenium, flavonoids, vitamin-like antioxidants such as coenzyme Q10 (CoQ10) and glutathione, and antioxidant enzymes such as superoxide dismutase (SOD), catalase, and glutathione peroxidase;
  • SOD superoxide dismutase
  • anti-inflammatory agents including, e.g., methyl salicylate, aspirin, ibuprofen, and naproxen.
  • Additional anti-inflammatories useful in topical applications include corticosteroids, such as, but not limited to, flurandrenolide, clobetasol propionate, halobetasol propionate, fluticasone propionate, betamethasone dipropionate, betamethasone benzoate, betamethasone valerate, desoximethasone, dexamethasone, diflorasone diacetate, mometasone furoate, amcinodine, halcinonide, fluocinonide, fluocinolone acetonide, desonide, triamcinolone acetonide, hydrocortisone, hydrocortisone acetate, fluoromethalone, methylprednisolone, and predinicarbate;
  • corticosteroids such as, but not limited to,
  • anesthetics that can be delivered locally including benzocaine, butamben, butamben picrate, cocaine, procaine, tetracaine, lidocaine and pramoxine hydrochloride;
  • analgesics such as ibuprofen, diclofenac, capsaicin, and lidocaine;
  • Non-limiting examples are micanazole, clotrimazole, butoconazole, fenticonasole, tioconazole, terconazole, sulconazole, fluconazole, haloprogin, ketonazole, ketoconazole, oxinazole, econazole, itraconazole, torbinafine, nystatin and griseofulvin;
  • antibiotics such as erythromycin, clindamycin, synthomycin, tetracycline, metronidazole and the like;
  • anti-viral agents including famcyclovir, valacyclovir and acyclovir;
  • anti-parasitic agents such as scabicedes, such as permethrin, crotamiton, lindane and ivermectin;
  • anti-infectious and anti-acne agents including benzoyl peroxide, sulfur, resorcinol and salicylic acid;
  • enzymes and co-enzymes including co-enzyme Q10, papain enzyme, lipases, proteases, superoxide dismutase, fibrinolysin, desoxyribonuclease, trypsin, collagenase and sutilains;
  • anti-histamines including chlorpheniramine, brompheniramine, dexchlorpheniramine, tripolidine, clemastine, diphenhydramine, prometazine, piperazines, piperidines, astemizole, loratadine and terfonadine;
  • chemotherapeutic agents such as 5-fluorouracil, masoprocol, mechlorethamine, cyclophosphamide, vincristine, chlorambucil, streptozocin, methotrexate, bleomycin, dactinomycin, daunorubicin, coxorubicin and tamoxifen; and
  • the products of this invention can also contain, for example, the following dyes, colorants or pigments: lactoflavin (riboflavin), beta-carotene, riboflavin-5′-phosphate, alpha-carotene, gamma-carotene, cantaxanthin, erythrosine, curcumin, quinoline yellow, yellow orange S, tartrazine, bixin, norbixin (annatto, orlean), capsanthin, capsorubin, lycopene, beta-apo-8′-carotenal, beta-apo-8′-carotenic acid ethyl ester, xantophylls (flavoxanthin, lutein, cryptoxanthin, rubixanthin, violaxanthin, rodoxanthin), fast carmine (carminic acid, cochineal), azorubin, cochineal red A (Ponceau 4 R), beetroot red, betanin, antho
  • extracts for example paprika extract, black carrot extract, red cabbage extract
  • so-called aluminum lakes FD & C Yellow 5 Lake, FD & C Blue 2 Lake, FD & C Blue 1 Lake, Tartrazine Lake, Quinoline Yellow Lake, FD & C Yellow 6 Lake, FD & C Red 40 Lake, Sunset Yellow Lake, Carmoisine Lake, Amaranth Lake, Ponceau 4R Lake, Erythrosyne Lake, Red 2G Lake, Allura Red Lake, Patent Blue V Lake, Indigo Carmine Lake, Brilliant Blue Lake, Brown HT Lake, Black PN Lake, Green S Lake and mixtures thereof.
  • the present invention also contemplates the incorporation of one or more adjunct materials including solvent, emollients, solubility modifiers, density modifiers, stabilizers, viscosity modifiers, pH modifiers, or any combination thereof. These modifiers can be present in the aqueous or oil phase.
  • the one or more adjunct material may be added in the amount of from 0.01% to 25% (e.g., from 0.5% to 10%) by weight of the flavor nanoemulsion.
  • solvent Preferable solvent materials are hydrophobic and miscible with the active materials. Solvents increase the compatibility of various active materials, increase the overall hydrophobicity of the mixture containing the active materials, influence the vapor pressure, or serve to structure the mixture. It should be noted that selecting a solvent and active material with high affinity for each other will result in improvement in stability.
  • Exemplary solvents are triglyceride oil, mono and diglycerides, mineral oil, silicone oil, diethyl phthalate, polyalpha olefins, castor oil, isopropyl myristate, mono-, di- and tri-esters and mixtures thereof, fatty acids, and glycerine.
  • the fatty acid chain can range from C 4 -C 26 and can have any level of unsaturation.
  • one of the following solvents can be used: capric/caprylic triglyceride known as NEOBEE M5 (Stepan Corporation); the CAPMUL series by Abitec Corporation (e.g., CAPMUL MCM); isopropyl myristate; fatty acid esters of polyglycerol oligomers, e.g., R 2 CO—[OCH 2 —CH(OCOR 1 )—CH 2 O—] n , where R 1 and R 2 can be H or C 4 -C 26 aliphatic chains, or mixtures thereof, and n ranges between 2 and 50, preferably 2 and 30; nonionic fatty alcohol alkoxylates like the NEODOL surfactants by BASF; the dobanol surfactants by Shell Corporation or the BIO-SOFT surfactants by Stepan, wherein the alkoxy group is ethoxy, propoxy, butoxy, or mixture
  • ester oils have at least one ester group in the molecule.
  • One type of common ester oil useful in the present invention are the fatty acid mono and polyesters such as cetyl octanoate, octyl isonanoanate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glycerol monostearate, glycerol distearate, glycerol tristearate, alkyl lactate, alkyl citrate and alkyl tartrate; sucrose ester and polyesters, sorbitol ester, and the like.
  • a second type of useful ester oil is predominantly composed of triglycerides and modified triglycerides.
  • These include vegetable oils such as jojoba, soybean, canola, sunflower, safflower, rice bran, avocado, almond, olive, sesame, persic, castor, coconut, and mink oils.
  • Synthetic triglycerides can also be employed provided they are liquid at room temperature.
  • Modified triglycerides include materials such as ethoxylated and maleated triglyceride derivatives provided they are liquids.
  • Proprietary ester blends such as those sold by FINETEX as FINSOLV are also suitable, as is ethylhexanoic acid glyceride.
  • a third type of ester oil is liquid polyester formed from the reaction of a dicarboxylic acid and a diol.
  • polyesters suitable for the present invention are the polyesters marketed by EXXONMOBIL under the trade name PURESYN ESTER.
  • Triglycerides and modified triglycerides as emollients include vegetable oils such as jojoba, soybean, canola, sunflower, safflower, rice bran, avocado, almond, olive, sesame, persic, castor, coconut, and mink oils.
  • Ester oils have at least one ester group in the molecule.
  • One type of common ester oil useful in the present invention are the fatty acid mono and polyesters such as cetyl octanoate, octyl isonanoanate, myristyl lactate, cetyl lactate, isopropyl myristate, myristyl myristate, isopropyl palmitate, isopropyl adipate, butyl stearate, decyl oleate, cholesterol isostearate, glycerol monostearate, glycerol distearate, glycerol tristearate, alkyl lactate, alkyl citrate and alkyl tartrate.
  • polyester oil as a liquid polyester formed from the reaction of a dicarboxylic acid and a diol.
  • polyesters suitable for the present invention are the polyesters marketed by ExxonMobil under the trade name PURESYN ESTER®, hydrophobic plant extracts.
  • Silicones include, for example, linear and cyclic polydimethylsiloxanes, amino-modified, alkyl, aryl, and alkylaryl silicone oil.
  • Solubility modifiers include surfactants (e.g., SLS and Tween 80), acidic compounds (e.g., mineral acids such as sulfuric acid, hydrochloric acid, nitric acid, and phosphoric acid, and carboxylic acids such as acetic acid, citric acid, gluconic acid, glucoheptonic acid, and lactic acid), basic compounds (e.g., ammonia, alkali metal and alkaline earth metal hydroxides, primary, secondary, or tertiary amines, and primary, secondary, or tertiary alkanolamines), ethyl alcohol, glycerol, glucose, galactose, inositol, mannitol, glactitol, adonitol, arabitol, and amino acids.
  • surfactants e.g., SLS and Tween 80
  • acidic compounds e.g., mineral acids such as sulfuric acid, hydrochloric acid, n
  • Density modifiers The density of the flavor oil droplets and the flavor nanoemulsion can be adjusted so that the nanoemulsion has a substantially uniform distribution using known density modifiers or technologies such as those described in Patent Application Publications WO 2000/059616, EP 1 502 646, and EP 2 204 155.
  • Suitable density modifiers include hydrophobic materials and materials having a desired molecular weight (e.g., higher than about 12,000), such as silicone oils, petrolatums, vegetable oils, especially sunflower oil and rapeseed oil, and hydrophobic solvents having a desired density (e.g., less than about 1,000 Kg/m3 at 25° C., such as limonene and octane.
  • a stabilizer e.g., a colloidal stabilizer
  • colloidal stabilizers are polyvinyl alcohol, cellulose derivatives such hydroxyethyl cellulose, polyethylene oxide, copolymers of polyethylene oxide and polyethylene or polypropylene oxide, or copolymers of acrylamide and acrylic acid.
  • Viscosity control agents e.g., suspending agents
  • which may be polymeric or colloidal e.g., modified cellulose polymers such as methylcellulose, hydoxyethylcellulose, hydrophobically modified hydroxyethylcellulose, and cross-linked acrylate polymers such as Carbomer, hydrophobically modified polyethers
  • silicas either hydrophobic or hydrophilic, can be included at a concentration from 0.01 to 20%, more preferable from 0.5 to 5%, by the weight of the flavor nanoemulsion.
  • hydrophobic silicas include silanols, surfaces of which are treated with halogen silanes, alkoxysilanes, silazanes, and siloxanes, such as SIPERNAT D17, AEROSIL R972 and R974 available from Degussa.
  • exemplary hydrophilic silicas are AEROSIL 200, SIPERNAT 22S, SIPERNAT 505 (available from Degussa), and SYLOID 244 (available from Grace Davison).
  • pH modifiers include metal hydroxides (e.g., LiOH, NaOH, KOH, and Mg(OH)2), metal carbonates and bicarbonates (CsCO3 Li2CO3, K2CO3, NaHCO3, and CaCO3), metal phosphates/hydrogen phosphates/dihydrogen phosphates, metal sulfates, ammonia, mineral acids (HCl, H2SO4, H3PO4, and HNO3), carboxylic acids (e.g., acetic acid, citric acid, lactic acid, benzoic acid, and sulfonic acids), and amino acids.
  • metal hydroxides e.g., LiOH, NaOH, KOH, and Mg(OH)2
  • metal phosphates/hydrogen phosphates/dihydrogen phosphates metal sulfates
  • ammonia mineral acids
  • mineral acids HCl, H2SO4, H3PO4, and
  • the level of the adjunct materials can be present at a level of 0.01 to 25% (e.g., from 0.5% to 10%) or greater than 10% (e.g., greater than 30% and greater than 70%).
  • a flavor nanoemulsion of this invention i.e., Emulsion I, was prepared following the procedure described below.
  • aqueous phase was obtained by dissolving 420 grams of sorbitol, 170 grams of glycerin, and 172 grams of propylene glycol in 180 grams of water, followed by adding 25 grams of TweenTM 60 (a polyethoxylated sorbitan fatty acid ester, commercially available from Croda, Edison, NJ) under high shear mixing using the Silverson high shear mixer, Model L4RT, (SILVERSON) at 6,500 rpm for 3 minutes.
  • TweenTM 60 a polyethoxylated sorbitan fatty acid ester, commercially available from Croda, Edison, NJ
  • an oil phase was prepared by mixing 3 grams standard fluid lecithin (HLB of about 4) and 30 grams of lemon flavor (International Flavors and Frances, Union Beach, NJ).
  • a pre-emulsion was formed by mixing the oil and aqueous phases under high shear mixing at 6,500 rpm for 3 minutes.
  • the pre-emulsion was further processed in a high-pressure microfluidizer (Model M-110P, Microfluidics, Westwood, MA) for three passes at 5,000 psi to obtain 1,000 grams of Emulsion I.
  • Emulsion I had a water activity of 0.53.
  • Emulsion II Another nanoemulsion of this invention, Emulsion II, was prepared following the same procedure as Emulsion I, except that 3 grams of enzyme modified lecithin SOLEC K-EML (commercially available from DuPont Nutrition & Health, St. Louis, Mo., USA, HLB of about 8) was used instead of standard fluid lecithin.
  • SOLEC K-EML enzyme modified lecithin SOLEC K-EML
  • Comparative Emulsion I′ was prepared following the same procedure as Emulsion I, except that no standard liquid lecithin was used and additional 3 grams of glycerin was added so that the total weight of the emulsion remained 1000 grams.
  • Comparative Emulsion II′ was prepared following the same procedure as Emulsion I, except that (i) 24 grams of enzyme modified lecithin, ALCOLEC C LPC20 (America Lecithin Company, Oxford, CT, USA) was used instead of TweenTM 60, (ii) the amount of standard liquid lecithin was reduced to 2.4 grams, and (iii) the amount of glycerin was increased to 171.6 grams.
  • ALCOLEC C LPC20 America Lecithin Company, Oxford, CT, USA
  • Comparative Emulsion III′ was prepared following the same procedure as Emulsion I, except that (i) 35 grams of fractionated lecithin, ALCOLEC PC75 (America Lecithin Company, Oxford, CT, USA) was used instead of TweenTM 60, (ii) the amount of standard fluid lecithin was reduced to 2.4 grams, and (iii) the amount of glycerin was reduced to 160.6 grams.
  • ALCOLEC PC75 America Lecithin Company, Oxford, CT, USA
  • a beverage of this invention i.e., Beverage A
  • Beverage A was prepared following the procedure described below. More specifically, 0.1% (wt/vol) of Emulsion I was added to an alcoholic beverage solution (8% alcohol), which was prepared by diluting an alcoholic syrup with water at a ratio of 1:3 ratio (syrup:water).
  • the alcoholic syrup formula is given in Table 2 below.
  • Turbidities of the drink were measured at time zero and after 1 day using a turbidimer (HACH Model 2100Q0) with the unit of Nephelometric Turbidity Units (“NTU”) specified by United States Environment Protection Agency. The measurement was carried out following the procedure described in the “Turbidity Measurement” section of the Owner Instruction Manual of the turbidimeter. The results are shown in Table 3 below.
  • Beverage B was prepared following the same procedure as Beverage A except that Emulsion II was used instead of Emulsion I.
  • Comparative Beverages A′, B′, and B′′ were prepared using Comparative Emulsion I′, II′, and III′, respectively.
  • each of Beverages A and B of this invention unexpectedly, has a turbidity much lower either at time zero or after one day than the comparatives.
  • a beverage of this invention i.e., Beverage C
  • Beverage C was prepared following the procedure described below. More specifically, 0.1% (wt/vol) of Emulsion I was mixed with a non-alcoholic beverage solution, which was prepared with the formulation shown in Table 4 below.
  • Turbidities of the Beverage H were measured at zero time and after 1 day.
  • Beverage D of this invention was prepared following the same procedure as Beverage C except that Emulsion II was used instead of Emulsion I.
  • Comparative Beverage C′ was prepared following the same procedure as Beverage C except that Comparative Emulsion I′ was used instead of Emulsion III.
  • Emulsion III of this invention was prepared following the same procedure as Emulsion II, except that 3 grams (instead of 25 grams) of TweenTM 60 was used.
  • the ratio between polyethoxylated sorbitan fatty acid ester TweenTM 60 and lecithin was 1:1, and the ratio between the polyethoxylated sorbitan fatty acid ester to the flavor oil at 1:10.
  • the amount of glycerin was increased accordingly to maintain the final product weight of 1000 grams.
  • Emulsion IV of this invention was prepared following the same procedure as Emulsion II, except that 6 grams (instead of 25 grams) of TweenTM 60 was used.
  • the ratio between polyethoxylated sorbitan fatty acid ester TweenTM 60 and lecithin was 2:1, and the ratio between the polyethoxylated sorbitan fatty acid ester to the flavor oil at 1:5.
  • the amount of glycerin was increased accordingly to maintain the final product weight of 1000 grams.
  • Emulsion V of this invention was prepared following the same procedure as Emulsion II, except that 30 grams (instead of 25 grams) of TweenTM 60 was used.
  • the ratio between polyethoxylated sorbitan fatty acid ester TweenTM 60 and lecithin was 10:1, and the ratio between the polyethoxylated sorbitan fatty acid ester to the flavor oil at 1:1.
  • the amount of glycerin was decreased accordingly to maintain the final product weight of 1000 grams.
  • Emulsion VI of this invention was prepared following the same procedure as Emulsion II, except that 60 grams (instead of 25 grams) of TweenTM 60 was used.
  • the ratio between polyethoxylated sorbitan fatty acid ester TweenTM 60 and lecithin was 20:1, and the ratio between the polyethoxylated sorbitan fatty acid ester to the flavor oil at 2:1.
  • the amount of glycerin was decreased accordingly to maintain the final product weight of 1000 grams.
  • Beverages E, F, G, and H of this invention were prepared using Emulsion III, IV, V, and VI, respectively, following the procedure described in Example 3 above except that different emulsions were used.
  • Emulsion VII of this invention was prepared following the same procedure as Emulsion II, except that (i) 12.5 grams of TweenTM 60 and 12.5 grams of TweenTM 80 were used instead of 25 grams of TweenTM 60.
  • Emulsion VIII of this invention was prepared following the same procedure as Emulsion II, except that (i) 12.5 grams of TweenTM 60 and 12.5 grams of TweenTM 20 were used instead of 25 grams of TweenTM 60.
  • Emulsion IX of this invention was prepared following the same procedure as Emulsion II, except that (i) 12.5 grams of TweenTM 20 and 12.5 grams of TweenTM 80 were used instead of 25 grams of TweenTM 60 and (ii) the amount of glycerin.
  • Beverages J, K, and L of this invention were prepared using Emulsion VII, VIII, and IX, respectively following the procedure described in Example 4 above. The turbidities of these three beverages were measured. The results are shown in Table 7 below along with Beverage B.
  • the four beverages each had a turbidity of less than 2 NTU both at time 0 and after 1 day.
  • Emulsion X of this invention was prepared following the same procedure as Emulsion II, except that 30 grams of water-dispersible antifoamer HI MAR S-010 FG K (10% silicone emulsion, Hi-Mar Specialty Chemicals, L.L.C., Milwaukee, Wis., USA) was added in the aqueous phase after high-shear mixing but prior to the high-pressure homogenization. The amount of glycerin was reduced by 30 grams.
  • water-dispersible antifoamer HI MAR S-010 FG K 10% silicone emulsion, Hi-Mar Specialty Chemicals, L.L.C., Milwaukee, Wis., USA
  • Emulsion XI of this invention was prepared following the same procedure as Emulsion II, except that 5 grams of oil-soluble antifoamer XIAMETER ACP-1500 (Dow Corning Corporation, Auburn, Mich., USA) was added in the flavor oil phase prior to high-shear mixing. The amount of glycerin was reduced by 5 grams. The pre-emulsion was further processed in a high-pressure homogenization for three passes at 7,000 psi.
  • Non-Alcoholic Beverages Prepared from Emulsion X and XI
  • Beverages M and N of this invention were prepared using Emulsion X and XI, respectively, following the same procedure as Beverage C except that different emulsions were used. Turbidities of Beverage S and Beverage T were measured and are shown in Table 8 below.
  • Emulsion XII of this invention was prepared following the same procedure as Emulsion I, except that (i) 17 grams of TweenTM 80 instead of 25 grams of TweenTM 60 were used and (ii) the amount of glycerin was increased to 250 grams and (iii) the amount of propylene glycol was reduced to 100 grams.
  • Emulsion XII had a water activity of 0.53 as measured with an AquaLab dew point water activity meter.
  • Beverage O of this invention was prepared following the same procedure as Beverage C except that Emulsion XII was used instead of Emulsion I.
  • Comparative Emulsion XII was prepared following the same procedure as Emulsion I, except that 15 grams of sucrose monopalmitate P90 (Commercially available from Compass Foods, Singapore) was used instead of TweenTM 60 and (ii) the amount of glycerin was increased to 252 grams and (iii) the amount of propylene glycol was reduced to 100 grams.
  • sucrose monopalmitate P90 Commercially available from Compass Foods, Singapore
  • Comparative Beverage O′ was prepared following the same procedure as Beverage C except that Comparative Emulsion XII was used instead of Emulsion I.
  • Beverage O and Comparative Beverage O′ were tasted for stability. The results showed that Beverage O was unexpectedly stable for 16 weeks when being stored at 37° C., which is equivalent to the storage for 16 months at room temperature. By contrast, Comparative Beverage O′ became unstable after 6 weeks when being stored at 37° C.
  • flavor nanoemulsion to prepare a flavor nanoemulsion, one skilled in the art can choose different flavors, solvents, contents and ratios of polyethoxylated sorbitan fatty acid esters and lecithins, co-solvents, and the load of flavors in beverages. Further, a skilled person can also choose other adjunct materials and suitable stabilizing agents.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • General Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Non-Alcoholic Beverages (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Edible Oils And Fats (AREA)
  • Tea And Coffee (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US15/518,595 2014-10-20 2015-10-20 Flavor nanoemulsions and methods of preparing the same Abandoned US20170247647A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US15/518,595 US20170247647A1 (en) 2014-10-20 2015-10-20 Flavor nanoemulsions and methods of preparing the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201462065865P 2014-10-20 2014-10-20
US201562197919P 2015-07-28 2015-07-28
PCT/US2015/056470 WO2016064883A1 (en) 2014-10-20 2015-10-20 Flavor nanoemulsions and methods of preparing the same
US15/518,595 US20170247647A1 (en) 2014-10-20 2015-10-20 Flavor nanoemulsions and methods of preparing the same

Publications (1)

Publication Number Publication Date
US20170247647A1 true US20170247647A1 (en) 2017-08-31

Family

ID=55761402

Family Applications (3)

Application Number Title Priority Date Filing Date
US15/520,087 Active 2035-12-01 US12256753B2 (en) 2014-10-20 2015-10-20 Metastable, translucent flavor nanoemulsion and methods of preparing the same
US15/518,595 Abandoned US20170247647A1 (en) 2014-10-20 2015-10-20 Flavor nanoemulsions and methods of preparing the same
US15/520,237 Active 2038-01-10 US11388907B2 (en) 2014-10-20 2015-10-20 Lysolecithin compositions and their use

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US15/520,087 Active 2035-12-01 US12256753B2 (en) 2014-10-20 2015-10-20 Metastable, translucent flavor nanoemulsion and methods of preparing the same

Family Applications After (1)

Application Number Title Priority Date Filing Date
US15/520,237 Active 2038-01-10 US11388907B2 (en) 2014-10-20 2015-10-20 Lysolecithin compositions and their use

Country Status (7)

Country Link
US (3) US12256753B2 (es)
EP (4) EP3590352B1 (es)
CN (6) CN107105694A (es)
BR (3) BR112017008161A2 (es)
ES (2) ES2866179T3 (es)
MX (3) MX384380B (es)
WO (3) WO2016064883A1 (es)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180094008A1 (en) * 2013-10-30 2018-04-05 Cargill, Incorporated Method for Purification of Lecithin
JP2019129808A (ja) * 2018-01-31 2019-08-08 三栄源エフ・エフ・アイ株式会社 香味増強剤、ならびに該増強剤および香料を含有する組成物
CN111278288A (zh) * 2017-08-23 2020-06-12 米格尔·恩里克·耶稣·马尔纳蒂·拉莫斯 用于生产保存新鲜或微加工食品用包封天然抗氧化剂的纳米乳剂的方法以及由此生产的乳剂
US20210030027A1 (en) * 2018-03-23 2021-02-04 Suntory Holdings Limited Aroma-free pear juice
CN113543651A (zh) * 2019-12-16 2021-10-22 弗门尼舍有限公司 用于饮料和个人护理应用的风味组合物
US20220071237A1 (en) * 2016-04-01 2022-03-10 Dsm Ip Assets B.V. Beverages comprising stable granules of milled lutein
CN114340402A (zh) * 2019-09-04 2022-04-12 百事可乐公司 用于制备透明乳液的方法
US20220110353A1 (en) * 2019-01-25 2022-04-14 Firmenich Sa Liquid concentrate delivery system
US20220287319A1 (en) * 2019-07-31 2022-09-15 Societe Des Produits Nestle S.A. Plant-based milk alternative with new taste experience
US20230049975A1 (en) * 2019-12-27 2023-02-16 Suntory Holdings Limited Beverage containing dispersed plant oil
WO2023062341A1 (en) * 2021-10-14 2023-04-20 Diageo Great Britain Limited Nanoemulsion for a beverage
WO2023212263A1 (en) * 2022-04-28 2023-11-02 Virtue Labs, LLC Photochemical hair styling methods and related compositions
US11825868B2 (en) 2019-11-18 2023-11-28 Hapy Sweet Bee Ltd Sweetener composition
US11839227B2 (en) 2019-11-18 2023-12-12 Hapy Sweet Bee Ltd Sweetener composition
US20240366702A1 (en) * 2022-05-14 2024-11-07 Syncotrance, LLC Modulation of solubility, palatability, absorption, and bioavailability of mitragyna speciosa-derived compounds for oral and buccal delivery
FR3153242A1 (fr) * 2023-09-27 2025-03-28 Laboratoire SHADELINE Nanoemulsions permettant une biodisponibilite amelioree de substances actives

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11247964B2 (en) * 2009-05-01 2022-02-15 Rrip, Llc Method of processing phospholipid based lipid materials
JP2019514386A (ja) * 2016-04-29 2019-06-06 ピュラトス・エヌブイＰｕｒａｔｏｓ Ｎｖ 改良されたベーカリー製品
ES3010116T3 (en) 2016-06-16 2025-04-01 Novozymes As Reduction of phospholipids in phospholipid-containing oil material
JP6953811B2 (ja) * 2017-06-12 2021-10-27 ライオン株式会社 口腔用組成物及び口腔内常在菌の生育促進剤
MX2021006320A (es) * 2018-12-17 2021-08-11 Givaudan Sa Metodo para contrarrestar el mal olor en una lavadora que comprende la adicion de un precursor de fragancia.
CN110564786B (zh) * 2019-08-02 2022-06-03 大渔华创(广州)海洋生物科技有限公司 一种epa/dha型溶血磷脂组合物及其制备方法
CN111996221B (zh) * 2020-08-31 2022-03-29 陕西科技大学 一种酶法制备sn2-LPC的方法
EP4175484B1 (en) * 2020-12-18 2024-12-04 Firmenich SA Flavor compositions for beverage and personal care applications
JP2024510700A (ja) * 2021-03-25 2024-03-11 フイルメニツヒ ソシエテ アノニム 飲料およびパーソナルケア用途のフレーバー組成物
KR102882807B1 (ko) * 2021-07-16 2025-11-10 주식회사 닥스메디 레시틴 효소반응물 및 이를 유효성분으로 포함하는 구강 건강 소재 및 제품
CN114931211A (zh) * 2022-03-22 2022-08-23 江西科技师范大学 一种橙皮苷-乳清蛋白基鱼油纳米乳的制备方法
FR3150815A1 (fr) * 2023-07-03 2025-01-10 Terra Cosmetics Agent emulsifiant pour la preparation de compositions topiques
WO2025189414A1 (en) * 2024-03-14 2025-09-18 Ldc (Shanghai) Animal Nutrition Technology Co., Ltd. Methods and systems for preparing lysolecithin

Family Cites Families (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3291614A (en) * 1958-03-03 1966-12-13 Nat Dairy Prod Corp Soluble dry milk product and a method of producing the same
AT277461B (de) 1968-04-17 1969-12-29 Nattermann & Cie Arzneimittelg Verfahren zur Herstellung eines neuen Lysolecithingemisches
US4518615A (en) 1983-08-23 1985-05-21 Warner-Lambert Company Non-adhesive chewing gum base composition
US4721620A (en) 1986-04-01 1988-01-26 Warner-Lambert Company Polyvinylacetate bubble gum base composition
US5093136A (en) 1991-05-08 1992-03-03 Nabisco Brands, Inc. Dual gum base bubble gum
US5266336A (en) 1991-11-12 1993-11-30 Wm. Wrigley Jr. Company High flavor impact non-tack chewing gum with reduced plasticization
US5635206A (en) * 1994-01-20 1997-06-03 Hoffmann-La Roche Inc. Process for liposomes or proliposomes
NL9400757A (nl) * 1994-05-06 1995-12-01 Campina Melkunie Bv Door hydrolysaten gestabiliseerde hitte-stabiele olie-in-water emulsies.
US5601858A (en) 1994-12-29 1997-02-11 Warner-Lambert Company Non-stick chewing gum
US5716814A (en) * 1996-02-02 1998-02-10 Biomolecular Products, Inc. Methods for making lysophosphatidylcholine
JP3375259B2 (ja) 1996-11-27 2003-02-10 株式会社日立製作所 磁気ディスク装置
JP3853464B2 (ja) * 1997-04-08 2006-12-06 辻製油株式会社 植物性リゾレシチンの製造法
US6068997A (en) * 1999-03-01 2000-05-30 Kemin Industries, Inc. Method for the conversion of lecithin into lysolecithin
AU4213900A (en) 1999-04-07 2000-10-23 Petramec, Inc. Methods of making and using microcapsules with controlled density
CA2432998C (en) 2001-01-25 2010-12-07 Unilever Plc Microemulsions
US6902756B2 (en) 2001-04-02 2005-06-07 Firmenich Sa Transparent high oil loaded microemulsions
US6986709B2 (en) 2001-09-21 2006-01-17 Igt Gaming device having games with variable game functions
JP4044354B2 (ja) 2002-03-28 2008-02-06 日油株式会社 耐アルコール性、耐酸性、耐塩性を有する組成物および用途
EP1502646B1 (en) 2003-08-01 2016-07-13 The Procter & Gamble Company Microcapsules
US8628690B2 (en) * 2004-02-23 2014-01-14 The Texas A&M University System Nanoemulsion compositions and methods of use thereof
US7189544B2 (en) * 2004-04-09 2007-03-13 Cargill, Incorporated Enzymatic modification of lecithin
EP1598060A1 (en) * 2004-05-18 2005-11-23 Nestec S.A. Oil-in-water emulsion for delivery
JP5051631B2 (ja) 2005-03-14 2012-10-17 株式会社ビオメディクス 水分散用抽出物含有組成物及びそれを用いた飲料
JP5140592B2 (ja) * 2005-09-02 2013-02-06 フイルメニツヒ ソシエテ アノニム 脂肪酸の糖エステルを含む透明フレーバーマイクロエマルション
US9743680B2 (en) * 2005-10-14 2017-08-29 Wild Flavors, Inc. Microemulsions for use in food and beverage products
CA2629091A1 (en) * 2005-11-22 2007-05-31 Nestec S.A. Oil-in-water emulsion and its use for the delivery of functionality
EP2046144B1 (en) * 2006-07-31 2017-09-27 Wm. Wrigley Jr. Company Food product with an encapsulated lecithin material
US20100098821A1 (en) * 2006-09-25 2010-04-22 Bob Comstock Process for Solubilization of Flavor Oils
US20090285952A1 (en) 2006-11-08 2009-11-19 Kaneaki Sekikawa Transparent Emulsified Composition for Use in Beverages
JP2008212107A (ja) * 2007-03-07 2008-09-18 Sanei Gen Ffi Inc バターを含有する水中油型乳化物及びバター含有飲料
AU2008329540B2 (en) 2007-11-28 2014-03-27 Commonwealth Scientific And Industrial Research Organisation Nanoemulsions
US20090196972A1 (en) 2008-02-04 2009-08-06 Adelmo Monsalve-Gonzalez Natural Flavor Enhancement Compositions for Food Emulsions
CN102186862B (zh) * 2008-11-12 2017-10-17 阿彻丹尼尔斯米德兰德公司 卵磷脂与增塑剂的组合物及方法
CN101473998B (zh) * 2008-12-17 2011-09-28 华宝食用香精香料（上海）有限公司 缓释性桂叶油微乳、其制备方法及用途
EP2204155A1 (en) 2008-12-30 2010-07-07 Takasago International Corporation Fragrance composition for core shell microcapsules
JP5680275B2 (ja) 2009-01-20 2015-03-04 富士フイルム株式会社 エマルション組成物、該エマルション組成物を含む食品及び化粧品
EP2359698B1 (en) * 2010-01-22 2013-12-04 Symrise AG Compositions with a surfactant system comprising saponins, and lecithin
KR101622441B1 (ko) * 2010-03-23 2016-05-18 버런, 아이엔씨. 자당 지방산 에스테르를 포함하는 나노에멀전
CA2839993A1 (en) * 2011-06-20 2012-12-27 Nestec S.A. Emulsion comprising lyso-phospholipids
US20130064954A1 (en) 2011-09-08 2013-03-14 Maria Ochomogo Microemulsion Concentrates and Nanoemulsion Flavorant Compositions For Food Applications
GB201204377D0 (en) * 2012-03-13 2012-04-25 Givaudan Sa Composition
CN104379757B (zh) * 2012-06-13 2017-03-15 株式会社钟化 含磷脂组合物的制造方法及含磷脂组合物
JP5588048B1 (ja) 2013-06-17 2014-09-10 高田香料株式会社 乳化香料組成物

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20180094008A1 (en) * 2013-10-30 2018-04-05 Cargill, Incorporated Method for Purification of Lecithin
US10442827B2 (en) * 2013-10-30 2019-10-15 Cargill, Incorporated Method for purification of lecithin
US20220071237A1 (en) * 2016-04-01 2022-03-10 Dsm Ip Assets B.V. Beverages comprising stable granules of milled lutein
CN111278288A (zh) * 2017-08-23 2020-06-12 米格尔·恩里克·耶稣·马尔纳蒂·拉莫斯 用于生产保存新鲜或微加工食品用包封天然抗氧化剂的纳米乳剂的方法以及由此生产的乳剂
JP2019129808A (ja) * 2018-01-31 2019-08-08 三栄源エフ・エフ・アイ株式会社 香味増強剤、ならびに該増強剤および香料を含有する組成物
US20210030027A1 (en) * 2018-03-23 2021-02-04 Suntory Holdings Limited Aroma-free pear juice
US20220110353A1 (en) * 2019-01-25 2022-04-14 Firmenich Sa Liquid concentrate delivery system
US12490761B2 (en) * 2019-01-25 2025-12-09 Firmenich Sa Liquid concentrate delivery system
US20220287319A1 (en) * 2019-07-31 2022-09-15 Societe Des Produits Nestle S.A. Plant-based milk alternative with new taste experience
CN114340402A (zh) * 2019-09-04 2022-04-12 百事可乐公司 用于制备透明乳液的方法
EP4025068A4 (en) * 2019-09-04 2023-08-30 Pepsico Inc PROCESS FOR PRODUCTION OF TRANSPARENT EMULSIONS
US11825868B2 (en) 2019-11-18 2023-11-28 Hapy Sweet Bee Ltd Sweetener composition
US11839227B2 (en) 2019-11-18 2023-12-12 Hapy Sweet Bee Ltd Sweetener composition
CN113543651A (zh) * 2019-12-16 2021-10-22 弗门尼舍有限公司 用于饮料和个人护理应用的风味组合物
US20230049975A1 (en) * 2019-12-27 2023-02-16 Suntory Holdings Limited Beverage containing dispersed plant oil
WO2023062341A1 (en) * 2021-10-14 2023-04-20 Diageo Great Britain Limited Nanoemulsion for a beverage
JP2024536538A (ja) * 2021-10-14 2024-10-04 ディアジオ グレート ブリテン リミテッド 飲料用ナノエマルジョン
JP7656778B2 (ja) 2021-10-14 2025-04-03 ディアジオ グレート ブリテン リミテッド 飲料用ナノエマルジョン
WO2023212263A1 (en) * 2022-04-28 2023-11-02 Virtue Labs, LLC Photochemical hair styling methods and related compositions
US20240366702A1 (en) * 2022-05-14 2024-11-07 Syncotrance, LLC Modulation of solubility, palatability, absorption, and bioavailability of mitragyna speciosa-derived compounds for oral and buccal delivery
FR3153242A1 (fr) * 2023-09-27 2025-03-28 Laboratoire SHADELINE Nanoemulsions permettant une biodisponibilite amelioree de substances actives
WO2025068411A1 (fr) * 2023-09-27 2025-04-03 Laboratoire SHADELINE Nanoemulsions permettant une biodisponibilite amelioree de substances actives

Also Published As

Publication number Publication date
EP3209137A1 (en) 2017-08-30
EP3590352A1 (en) 2020-01-08
EP3209142A1 (en) 2017-08-30
MX384966B (es) 2025-03-14
MX2017005139A (es) 2017-12-04
EP3209146B1 (en) 2020-05-20
EP3209137A4 (en) 2018-05-23
BR112017008023A2 (pt) 2018-02-20
EP3209142A4 (en) 2018-04-04
MX384380B (es) 2025-03-14
BR112017008161A2 (pt) 2018-02-20
US12256753B2 (en) 2025-03-25
WO2016064828A1 (en) 2016-04-28
CN107105694A (zh) 2017-08-29
CN120660763A (zh) 2025-09-19
CN118240888A (zh) 2024-06-25
ES2866179T3 (es) 2021-10-19
WO2016064848A1 (en) 2016-04-28
WO2016064883A1 (en) 2016-04-28
EP3209137B1 (en) 2019-12-18
ES2811123T3 (es) 2021-03-10
EP3209146A4 (en) 2018-04-04
MX2017005138A (es) 2018-02-12
CN107072269A (zh) 2017-08-18
US20170311632A1 (en) 2017-11-02
US11388907B2 (en) 2022-07-19
MX2017005028A (es) 2017-12-04
EP3590352B1 (en) 2021-03-24
BR112017008067A2 (pt) 2018-02-20
CN120616104A (zh) 2025-09-12
US20180295852A1 (en) 2018-10-18
CN107105708A (zh) 2017-08-29
EP3209142B1 (en) 2019-12-04
EP3209146A1 (en) 2017-08-30

Similar Documents

Publication Publication Date Title
EP3209146B1 (en) Flavor nanoemulsions and methods of preparing the same
CN104114038B (zh) 乳剂组合物以及包含其的组合物
US20230217943A1 (en) Robust flavor emulsions
CN103284107A (zh) 含有脂肪酸的糖酯的透明香料微乳液
CN106929370A (zh) 酒精饮料用乳化香料组合物
Saari et al. Nano-based products in beverage industry
CN110049684A (zh) 大量含有萜烯系烃香料化合物的水包油型乳化香料组合物
CN113543651A (zh) 用于饮料和个人护理应用的风味组合物
ES2831324T3 (es) Composiciones de sabor secadas por pulverización sin propilenglicol y métodos para producir las mismas
WO2019107574A1 (ja) 乳化組成物
BR112021005213A2 (pt) sistema de distribuição de concentrado líquido
US20260041109A1 (en) Robust flavor emulsions
WO2024026225A1 (en) Robust flavor emulsions
EP4175484B1 (en) Flavor compositions for beverage and personal care applications
EP4333630A1 (en) Flavor nanoemulsions for beverage and personal care applications
AU2023332732A1 (en) Water-dispersible cannabinoid emulsion formulations, methods of making and applications
WO2019219589A1 (en) Composition
HK40005560A (en) Terpene-based hydrocarbon fragrance compound–rich oil-in-water type emulsified fragrance composition

Legal Events

Date Code Title Description
AS Assignment

Owner name: INTERNATIONAL FLAVORS AND FRAGRANCES INC., NEW YOR

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LEE, DANIEL KAIPING;WANG, CHII-FEN;YANG, YING;AND OTHERS;SIGNING DATES FROM 20170412 TO 20170418;REEL/FRAME:042081/0961

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION